Carbon To Carbon Unsaturation Between Ring Members Of The Five-membered Hetero Ring (e.g., Maleimide, Etc.) Patents (Class 548/548)
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Patent number: 4794190Abstract: Alpha-(4-maleimidophenyl)-alpha'-(4-isomaleimidophenyl) diisopropyl benzene, as a novel composition of matter. The compound, which may be used as a component of curable thermoset resins or as a unique, difunctional synthesis intermediate having non-symmetrical reactivity, may be prepared from the corresponding bis-maleamic acid by dehydrating at or below ordinary, ambient temperatures, using acetic anhydride or a similar dehydrating agent.Type: GrantFiled: January 28, 1987Date of Patent: December 27, 1988Assignee: Amoco CorporationInventors: Linda A. Domeier, Elke M. Clark
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Patent number: 4788295Abstract: Novel N-(meth)allyloxyphenylmaleimides are prepolymerized with at least one bis-imide and formulated, together with at least one imidazole compound, into thermosetting compositions useful for the production of a wide variety of shaped articles having improved mechanical properties.Type: GrantFiled: July 1, 1986Date of Patent: November 29, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Rakoutz, deceased
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Patent number: 4786738Abstract: A method for the production of maleimides, which comprises subjecting maleinamic acids to ring-closure imidation in an organic solvent capable of forming an azeotrope with water in the presence of an acid catalyst at a temperature in the range of 120.degree. to 250.degree. C. while removing the formed water in the form of an azeotrope with said organic solvent and thereafter purifying the produced maleimides.Type: GrantFiled: October 27, 1986Date of Patent: November 22, 1988Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuichi Kita, Kentaro Sakamoto, Masao Baba, Atsushi Okubo
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Patent number: 4783547Abstract: The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.Type: GrantFiled: April 18, 1986Date of Patent: November 8, 1988Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 4780546Abstract: A method for the production of maleimides, which comprises subjecting maleinamic acids to ring-closure imidation in an organic solvent capable of forming an azeotrope with water in the presence of an acid catalyst at a temperature in the range of 120.degree. C. to 250.degree. C. while removing the formed water in the form of an azeotrope with said organic solvent and thereafter purifying the produced maleimides.Type: GrantFiled: October 27, 1986Date of Patent: October 25, 1988Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.Inventors: Yuichi Kita, Kentaro Sakamoto, Masao Baba, Atsushi Okubo
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Patent number: 4777237Abstract: Novel, heat-stable imido polymers, well adopted, e.g., as coating or molding resins, comprise the polymerizates of (a) at least one N,N'-bismaleimide, (b) at least one diprimary diamine, and (c) at least one N-(meth)-allyloxyphenylmaleimide.Type: GrantFiled: November 13, 1986Date of Patent: October 11, 1988Assignee: Rhone-Poulenc Specialities ChimiquesInventors: Rene Dien, Michel Rakoutz
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Patent number: 4709052Abstract: A soil disease controlling agent for preventing and controlling diseases caused by pathogenic fungi living in soil, which comprises an effective amount of at least one of a 2-cycloalkenylamine derivative and its salts as an active ingredient, and at least one inert carrier or diluent.Type: GrantFiled: May 16, 1984Date of Patent: November 24, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroki Tomioka, Tadashi Ooishi, Junya Takahashi, Mitsuru Sasaki, Naonori Hirata
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Patent number: 4683276Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.Type: GrantFiled: October 1, 1985Date of Patent: July 28, 1987Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4680378Abstract: Polymerizable compositions are disclosed which comprises a mixture of (A) at least one thermosettable compound which simultaneously contains both a maleimide group or substituted maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and (B) at least one material containing a plurality of aromatic amine groups such as 4,4'-diaminodiphenylmethane. Also disclosed are mixtures of the above polymerizable compositions and (C) at least one other material selected from (1) aromatic polycyanates, (2) polymaleimides, (3) materials having an average of more than one vicinal epoxide group per molecule, (4) a polymerizable ethylenically unsaturated material and (5) any combination thereof. The cured, polymerized products are useful as coatings, structural or electrical laminates or composites, castings, and the like.Type: GrantFiled: October 1, 1985Date of Patent: July 14, 1987Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4675414Abstract: Aliphatic polyethers having at least two N-methylmaleimide groups chemica joined thereto by a carbonate linkage are provided and a method for making such compounds. The hydroxy-terminated aliphatic polyether, such as polypropylene glycol, is initially reacted with carbonyl chloride to form the chloroformate. The polyether chloroformate derivative is then reacted with N-hydroxymethylmaleimide yielding the bis or tris(maleimidomethyl)carbonate of said polyether.Type: GrantFiled: March 8, 1985Date of Patent: June 23, 1987Assignee: The United States of America as represented by the Secretary of the NavyInventors: Albert A. DeFusco, Eugene C. Martin
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Patent number: 4666935Abstract: Substituted maleimides of the formula in whichX represents hydrogen, chlorine or bromine,X.sup.1 represents chlorine or bromine,n represents 2, 3, 4 or 5 andR represents halogen, alkyl, optionally substituted aryl, aryloxy or cycloalkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, acyloxyalkyl, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, carboxyl, carbonylamino, hydroxyl, alkoxy, halogenoalkoxy, acyloxy, sulphonylamino, alkylsulphonyl, alkylmercapto, marcapto, acylmercapto, halogenoalkylmercapto, amino, mono- or di-alkylamino or acylamino andm represents 1, 2, 3, 4 or 5,which possess fungicidal activity.Type: GrantFiled: February 8, 1984Date of Patent: May 19, 1987Assignee: Bayer AktiengesellschaftInventors: Gerhard Marzolph, Heinz U. Blank, Paul Reinecke, Wilhelm Brandes, Gerd Hanssler
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Patent number: 4656292Abstract: 2,3-Dimethylmaleimido-alkyl or oxaalkyl haloacetates are useful in the preparation of polymers containing maleimide groups and quaternary ammonium groups which polymers are soluble in water. The polymers can be used as light-sensitive photographic recording materials which can be developed with water.Type: GrantFiled: June 17, 1985Date of Patent: April 7, 1987Assignee: Ciba-Geigy CorporationInventor: Martin Roth
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Patent number: 4645776Abstract: The new compound N-(dichlorofluoromethylthio)-3,4-dimethylmaleimide can be prepared by reacting 3,4-dimethylmaleimide with dichlorofluoromethanesulphenyl chloride in the presence of an acid-binding agent. N-(dichlorofluoromethylthio)-3,4-dimethylmaleimide is an active compound in microbicidal agents.Type: GrantFiled: April 9, 1985Date of Patent: February 24, 1987Assignee: Bayer AktiengesellschaftInventors: Engelbert Kuhle, Wilfried Paulus, Hermann Genth
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Patent number: 4642353Abstract: Photocrosslinkable polymers having an average molecular weight of at least 1,000 and side groups of the formula Ia and/or Ib ##STR1## in which R, R', R.sub.1, R.sub.2, A, E, Y and n are as defined in claim 1, are suitable, for example, for preparing solvent-resistant coatings on metals and, in particular, for preparing printing plates or printed circuits. The group of the formula Ia and/or Ib content is at least 0.5%, preferably 5-100%, based on the number of the polymer's recurring structural elements.Type: GrantFiled: February 20, 1986Date of Patent: February 10, 1987Assignee: Ciba-Geigy CorporationInventor: Joseph Berger
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Patent number: 4638078Abstract: The invention is a compound which comprises an amido alkenoic acid or a water-soluble salt thereof and and arylcyclobutene moiety, wherein the cyclobutene moiety is fused to the aryl radical, and wherein the amide nitrogen is connected to the aryl radical of the arylcyclobutenyl moiety by a direct bond or a bridging member.Type: GrantFiled: April 25, 1985Date of Patent: January 20, 1987Assignee: The Dow Chemical CompanyInventor: Robert A. Kirchhoff
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Patent number: 4599430Abstract: A process is provided for the nitrogenation of hydrocarbons, resulting in the production of cyclic imides and nitriles from hydrocarbons contacted with molecular oxygen and a nitrogenating agent, including ammonia or primary amines, in the presence of an oxidation catalyst containing variable valency metal oxides, in the vapor phase at elevated temperature.Type: GrantFiled: February 2, 1984Date of Patent: July 8, 1986Assignee: The Standard Oil CompanyInventors: Ernest C. Milberger, Eunice K. T. Wong
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Patent number: 4588786Abstract: A process for producing a water-soluble dicarboxylic acid imide compound which comprises adding a primary amine compound to an aqueous solution of a water-soluble salt of a dicarboxylic acid compound containing at least one dicarboxylic acid unit capable of forming a 5-membered cyclic acid imide linkage and heating the mixture to introduce an acid imide linkage into the molecule.Type: GrantFiled: October 5, 1984Date of Patent: May 13, 1986Assignee: Nippon Zeon Co., Ltd.Inventors: Hiromitsu Kadono, Tadao Natsuume
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Patent number: 4582849Abstract: Fungicidally active substituted maleic acid amides of the formula ##STR1## in which X is hydrogen, chlorine or bromine,X.sup.1 is chlorine or bromine,R is alkyl, optionally substituted aryl or optionally substituted aralkyl,R.sup.1 to R.sup.5 each independently is hydrogen, alkyl, optionally substituted aryl or optionally substituted aralkyl,R.sup.6 each independently is halogen, alkyl, optionally substituted aryl, optionally substituted cycloalkyl, alkoxy, sulphonylamine, halogenoalkyl, nitro, cyano, alkoxycarbonyl, alkylsulphonyl or carboxylamine,n is 0, 1, 2 or 3,m is 0, 1, 2 or 3,m+n is 0, 1, 2 or 3, andy is 0, 1, 2, 3, 4 or 5,with the exception of the compound in whichX and X.sup.1 are chlorine,m and y are 0,n is 1,R.sup.1, R.sup.4 and R.sup.5 are hydrogen, andR is methyl,and the compound in whichX and X.sup.1 are chlorine,m, n and y are 0,R.sup.1 is hydrogen, andR is phenyl.Type: GrantFiled: May 27, 1983Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Marzolph, Heinz U. Blank, Paul Reinecke, Wilhelm Brandes, Hans Scheinpflug
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Patent number: 4552890Abstract: A method of combatting fungi which comprises applying to fungi or a fungus habitat a fungicidally effective amount of at least one maleic acid N-aralkyl-imide of the formula ##STR1## in which X is hydrogen or halogen,Hal is halogen, andm is 2,3 or 4.Those compounds are new in whichHal is chlorine or bromine, andX is hydrogen or bromine if m is 2, orX is chlorine if m is 4.Type: GrantFiled: February 8, 1984Date of Patent: November 12, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Marzolph, Heinz U. Blank, Paul Reinecke, Wilhelm Brandes, Gerd Hanssler
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Patent number: 4537902Abstract: Novel 4-substituted-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.Type: GrantFiled: June 11, 1979Date of Patent: August 27, 1985Assignees: Merck & Co., Inc., Merck Sharp & Dohme (I.A.) Corp.Inventors: Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
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Patent number: 4532332Abstract: There are obtained from N-(hydroxypolyoxaalkylene)imidyl compounds and (meth)acrylic acid esters thereof homopolymers or copolymers with olefinically unsaturated comonomers. These polymers are photosensitive and are suitable as photographic recording material, as adhesives and as agents for surface coating.Type: GrantFiled: August 5, 1982Date of Patent: July 30, 1985Assignee: Ciba-Geigy CorporationInventor: Beat Muller
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Patent number: 4520206Abstract: A process for the preparation of maleimide by the vapor phase oxydehydrogenation of succinimide over a heterogeneous catalyst composed of copper, phosphorous, vanadium, molybdenum and oxygen is described.Type: GrantFiled: February 27, 1984Date of Patent: May 28, 1985Assignee: Ashland Oil, Inc.Inventor: Stephen S. Hupp
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Patent number: 4515965Abstract: A process for the preparation of maleimide by the vapor phase oxydehydrogenation of succinimide over an iron phosphate catalyst which may also contain one or more alkali metal and alkaline earth metal components is described.Type: GrantFiled: February 10, 1984Date of Patent: May 7, 1985Assignee: Ashland Oil, Inc.Inventor: Stephen S. Hupp
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Patent number: 4474968Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.Type: GrantFiled: November 14, 1980Date of Patent: October 2, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4460783Abstract: An ether imide of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and D are as defined in the specification produced by reacting a diamine with an ethylenically unsaturated dicarboxylic acid can give a composition together with one or more unsaturated polyesters, epoxy compounds, amines, and the like to give shaped articles excellent in flexibility and heat resistance.Type: GrantFiled: January 19, 1981Date of Patent: July 17, 1984Assignee: Hitachi, Ltd.Inventors: Akio Nishikawa, Masashi Shitara, Susumu Era, Toshiaki Fukushima, Hiroshi Suzuki, Hisashi Kohkame
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Patent number: 4458084Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.This case is a continuation of Ser. No. 906,175 filed May 15, 1978, now abandoned.Type: GrantFiled: November 14, 1981Date of Patent: July 3, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4458083Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.This case is a continuation of Ser. No. 906,175 filed May 15, 1978, now abandoned.Type: GrantFiled: November 14, 1980Date of Patent: July 3, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4458089Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.This case is a continuation of Ser. No. 906,175 filed May 15, 1978, now abandoned.Type: GrantFiled: November 14, 1980Date of Patent: July 3, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4431660Abstract: Novel 4-substituted-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.Type: GrantFiled: October 17, 1980Date of Patent: February 14, 1984Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
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Patent number: 4396516Abstract: This invention is a lubricant comprising an imide compound obtained by reacting a dibasic acid selected from the group consisting of succinic acid, maleic acid, glutaric acid and phthalic acid with a primary amine having a C.sub.8 -C.sub.18 hydrocarbon radical.The lubricant of the invention may be used in combination with a specified diamine derivative and known lubricant additives, and exhibits excellent lubricating properties.Type: GrantFiled: June 9, 1981Date of Patent: August 2, 1983Assignee: Nippon Oil Company, Ltd.Inventors: Hirotsugu Kinoshita, Hiroshi Uemura, Makoto Sekiya, Kazuyoshi Mitamura
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Patent number: 4332724Abstract: There is provided a process for the preparation of an amido or an ureido derivative of certain 4,5,6,7-tetrahydro-7-oxobenzo[b]thiophenes or certain 1,2,3,4-tetrahydro-4-oxonaphthalenes which can be employed as an animal growth regulant. The process comprises: oxidizing in the presence of a cobalt catalyst a compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a substituent selected from the group consisting of alkanoyl C.sub.1 -C.sub.7, halogen-substituted alkanoyl C.sub.1 -C.sub.7, carboalkoxy C.sub.1 -C.sub.4, ##STR2## and ##STR3## R.sub.3 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ; R.sub.4 is selected from the group consisting of hydr ogen, alkyl C.sub.1 -C.sub.8, alkanoyl C.sub.2 -C.sub.4, halogen-substituted alkanoyl (C.sub.2 -C.sub.Type: GrantFiled: November 16, 1977Date of Patent: June 1, 1982Assignee: American Cyanamid Co.Inventors: Terence J. Bentley, William H. Gastrock, Goro Asato